This research proposal provides initial results that substantiate the utility of Mo-catalyzed Asymmetric Ring- Opening Cross-Metathesis (AROCM) in the synthesis of chiral pyrans and piperidines, two structural motifs present in myriad biologically important natural products. In addition, we outline our plans for extending this methodology to a variety of oxa- and aza-bridged [3.2.1] bicyclic substrates, and extending this methodology to olefin cross partners that can be readily functionalized. Currently, there are no other known methods for setting the chirality of 2,6-cis-substituted-pyrans and -piperidines through metathesis. The Mo-catalyzed AROCM to form chiral piperidines will be applied to the target oriented total synthesis of lobeline, a biologically active natural product part of a class of alkaloids isolated from the herb Lobelia inflate. [unreadable] [unreadable]